Organic Materials (May 2022)

Synthesis and C60 Binding of Aza[10]CPP and N-Methylaza[10]CPP

  • Fabian Schwer,
  • Simon Zank,
  • Markus Freiberger,
  • Ramandeep Kaur,
  • Stefan Frühwald,
  • Craig C. Robertson,
  • Andreas Görling,
  • Thomas Drewello,
  • Dirk M. Guldi,
  • Max von Delius

DOI
https://doi.org/10.1055/a-1814-7686
Journal volume & issue
Vol. 4, no. 02
pp. 7 – 17

Abstract

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Abstract Within the growing family of strained carbon nanohoops and nanobelts, [10]CPP arguably offers the best compromise between synthetic accessibility and strong binding affinity for C60. In this work, we report the synthesis of two nitrogen-containing analogues of [10]CPP and we systematically compare the structure, optoelectronic properties and C60 binding affinities of this small set of structurally similar macrocycles. While Aza[10]CPP outcompetes the parent compound by approximately one order of magnitude with respect to C60 binding, we found that the reverse was true for the methylaza analogue. Transient absorption studies showed that photo-induced electron transfer occurred readily from [10]CPP and its aza-analogue to an encapsulated C60 guest. Formation of a charge-separated complex was not observed however for the N-methylated derivative. These insights will prove useful for further applications of strained nanohoops in supramolecular chemistry and organic electronics.

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